Comparative Study on the Reaction of Organophosphorus Reagents with Vanillin from Moringa Oleifera Plant. Synthesis of Phosphoranylidenepyranone, Dioxaphospholane and Butenethione Derivatives of Anticipated Antitumor Agents

Vanillin which can be isolated from Moringa oleifera plant was allowed to react with different nucleophilic organophosphorus reagents. Treatment of 4-hydroxy-3-methoxybenzaldehyde (vanillin) with the active phosphacumulene ylides (N-phenyliminovinylidene)- and (2-oxovinylidene)-triphenylphosphorane afforded the homocyclic phosphoranylidene-cyclobutylidenes. On the other hand, its reaction with the satabilized phosphoniumylide, acetylmethylenetriphenylphosphorane gave the corresponding butenone, which reacted with the active phosphacumulene to give finally the pyran derivative. Next, the phenyliminophenol derivative was obtained from the reaction of vanillin with the iminophosphorane. Moreover, dioxaphospholane oxide was isolated from the reaction of vanillin with hexamethylphosphorus triamide. Finally, the butenethione was generated from the reaction of Japanese reagent with vanillin.